Process for decabromodiphenylalkane predominant product

• US 5,124,496 A
• Filed: 11/01/1990
• Issued: 06/23/1992
• Est. Priority Date: 11/01/1990
• Status: Expired due to Term

• Current Assignee: Albemarle Corporation
• Original Assignee: Ethyl Corporation (Newmarket Corporation)
• Inventors: Hussain, Saadat, Davis, Robert L., McKinnie, Bonnie G., Templeton, Mark A.
• Primary Examiner(s): LONE, WERREN
• Application Number:
  US07/607,822
• Time in Patent Office: 600 Days
• Field of Search: 570/199, 570/206, 570/210, 570/208, 252/397, 252/399
• US Class Current: 570/210
• CPC Class Codes: C07C 17/12 in the ring of aromatic compounds
• CPC Class Codes: C07C 25/18 Polycyclic aromatic halogenated hydrocarbons

Abstract

This invention relates to a white or at least near white flame retardant product which is predominant in decarbromodiphenylalkane, and which product contains a minor amount of impurities; to a process for preparation of the flame retardant product; to a process for the removal of excess bromine from the product by use of a treatment solution and elevated temperature; and to macromolecular materials utilizing the product as a flame retardant.

Claims

1. A process for preparing a flame retardant product predominant in decabromodiphenylalkane, the process comprising:

forming a stirrable first reaction mass by feeding molten diphenylalkane to a reaction vessel to which a bromination catalyst and bromine had been previously charged;

maintaining the first reaction mass at a temperature in the range of from about 0°

C. to about reflux during the feeding;

subsequent to the feeding, separating the decabromodiphenylalkane predominant product from the bromine and catalyst;

forming a stirrable second reaction mass from the separated product and a treatment solution; and

maintaining the second reaction mass for a period of time and at a temperature which is sufficient to obtain the decabromodiphenylalkane predominant product.

2. The process of claim 1 wherein the diphenylalkane reactant is 1,2-diphenylethane.

3. The process of claim 1 wherein the product comprises 90⁺ weight percent decarbromodiphenylalkane.

4. The process of claim 3 wherein the decabromodiphenylalkane is decabromodiphenylethane.

5. The process of claim 1 wherein the amount of bromine charged provides from about 18 to about 23 moles of bromine per mole of diphenylalkane.

6. The process of claim 2 wherein the 1,2-diphenylethane is at a temperature in the range of from about 55°

C. to about 80°

C. when fed to the reaction vessel.

7. The process of claim 6 wherein the 1,2 diphenylethane is fed under a nitrogen atmosphere.

8. The process of claim 1 wherein the product is separated from the bromine solvent by filtering the first reaction mass and collecting the product as a wet cake.

9. The process of claim 1 wherein the second reaction mass is maintained at a temperature in the range of from about 180°

C. to about 300°

C. for a period of from about 1 to about 5 hours.

10. The process of claim 1 wherein the treatment solution is comprised of an ammonium hydroxide solution.

11. The process of claim 1 wherein the treatment solution is comprised of an aqueous mixture of Na₂ CO₃ and Na₂ SO₃ in a molar ratio of about 3:

1 of Na₂ CO₃ to Na₂ SO₃.

12. A process for preparing a flame retardant product predominant in decabromodiphenylethane, the process comprising:

forming a stirrable first reaction mass by feeding molten 1,2-diphenylethane to a reaction vessel to which a bromination catalyst and bromine had been previously charged, the molten 1,2-diphenylethane having a purity of at least 99.5 weight percent and being maintained under a non-oxidizing atmosphere prior to the feeding, and the bromine being charged in an amount which provides from about 18 to about 23 moles of bromine per mole of 1,2-diphenylethane fed;

maintaining the first reaction mass at a temperature in the range of from about 15°

C. to about reflux during the feeding;

separating the decabromodiphenylethane predominant product from the bromine and catalyst;

forming a stirrable second reaction mass from the separated product and a treatment solution; and

maintaining the second reaction mass for a period of time and at a temperature which is sufficient to obtain the decabromodiphenylethane predominant product.

13. The process of claim 12 wherein the product comprises at least 90⁺ weight percent decabromodiphenylethane and less than about 100 ppm excess bromine.

14. The process of claim 13 wherein the product is separated from the bromine solvent by filtering the first reaction mass and collecting the product as a wet cake.

15. The process of claim 14 wherein the treatment solution is comprised of an ammonium hydroxide solution.

16. The process of claim 15 wherein the treatment solution is comprised of an aqueous mixture of Na₂ CO₃ and Na₂ SO₃ in a molar ratio of about 3:

1 of Na₂ CO₃ to Na₂ SO₃.

17. The process of claim 16 wherein the temperature of the second reaction mass is in the range of from about 180°

to about 300°

C.

18. An ABS formulation containing a flame retardant amount of the product produced by the process of claim 17 and with or without Sb₂ O₂ as a flame retardant synergist being present in said formulation.

19. A HIPS formulation containing a flame retardant amount of the product produced by the process of claim 17 and with or without Sb₂ O₂ as a flame retardant synergist being present in said formulation.

20. A process for enhancing the purity of a decabromodiphenylalkane predominant product containing, at least initially, excess bromine, the process comprising:

a) forming a stirrable reaction mass, the reaction mass comprising a decabromodiphenylalkane predominant product containing excess bromine as an impurity, and a treatment solution; and

b) maintaining the reaction mass for a period of time and at a temperature which is sufficient to obtain the enhanced decabromodiphenylalkane predominant product containing less than about 100 ppm excess bromine.

21. The process of claim 20 wherein the decabromodiphenylalkane predominant product contains, at least initially, more than about 100 ppm excess bromine.

22. The process of claim 20 wherein the temperature is in the range of from about 180°

to about 350°

C.

23. The process of claim 22 wherein the treatment solution is comprised of an ammonium hydroxide solution.

24. The process of claim 22 wherein the treatment solution is comprised of an aqueous mixture of Na₂ CO₃ and Na₂ SO₃ in a molar ratio of about 3:

1 of Na₂ CO₃ to Na₂ SO₃.